30 Of The Funniest ‘Pictures From A Regrettable Past’ Shared By People Of Their “Cool” Teenage Years

As young teenagers, most of us had an experimental phase where we did crazy things with our hair and dressed even weirder thinking we looked hella ‘cool’. Looking back on photo albums is usually a cringe experience due to this, as reminders of our bad decisions come back to haunt us. 

#1 My Nickname Was “Ronald” In School

Image source: DannyDublin1975

#2 It Was The 80s. I Have No Other Excuse

Image source: owzleee

#3 My Brother And I, Late 90s

Image source: KFCCrocs

#4 I Guess Being Able To See Is Overrated

Image source: EmpireEmpire

#5 Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This

Image source: maybejolisa

#6 1987, We Loved The Cure, 7seconds, The Decedents, The Smiths, Etc. We Taped 120 Minutes Off Mtv Every Sunday Night From Midnight – 2 Am. I’m On The Far Left. Can Believe We Weren’t Blind In One Eye After All The Years With The Lopsided Haircuts

Image source: Acctgrrl

#7 Thanks To My Sister, I Completely Embraced Goth Culture In 1998

Image source: clumsychickadee__

#8 Oh College. I’ll Never Be This Cool Again

Image source: TrondroKely

#9 Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo

Image source: Kbeefydubbz

#10 Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t

Image source: tootyfruitysummerluv

#11 This Is So Long Ago And Yes I Worked At Hot Topic

Image source: dinosaurpixie

#12 My Teenage Years Are The Gift That Keeps On Giving

Image source: Toshhba

#13 Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999

Image source: thomASSpynchon

#14 1991 Obsessed With Michael Jordan

Image source: foshi22le

#15 Leave Some Ladies For The Rest Of Us

Image source: youruineverything

#16 My Senior Yearbook Photo. I Thought That Quote Was So Funny

Image source: 7fingersphil

#17 That Weird Al Early 00s Look

Image source: timconnery

#18 This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989

Image source: reddit.com

#19 Mom, It’s Not A Phase

Image source: inkmaster916

#20 2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam

Image source: symbolicthoughts

#21 You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!

Image source: tshaff138

#22 1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look

Image source: luckymama1990

#23 In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls

Image source: alexanfaye

#24 1999 Tony Hawk Phase (Yes, Those Are Shorts…)

Image source: zephsoph

#25 2003. I Smiled Like This In Every Picture Because I Thought It Looked “Natural.” I Swere I’ve Never Harmed Any Animals

Image source: NSMetroid

#26 My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet

Image source: artisticatrophy

#27 Y’all I Thought I Was Cool Taking These Photos For A Anti Bullying Campaign ? I Did Get In A Magazine Thought (It Was A Contest To Submit Photos For Their Stop Think Feel Initiative)

Image source: Infinitestripes95

#28 My “Date” To The Eighth Grade Dance

Image source: tamenesh

#29 1985, I’m Mr.gender Bender Glam Goth And Club Scene Regular. The Whole Time I Secretly Listened To Thrash Music Lol. Will I Ever Live It Down?!

Image source: Seanessey

#30 High School Art Class

Image source: minthotel